The Kentucky Derby has seen its fair share of upsets over the years as horse racing can be extremely unpredictable. In fact, the majority of times the expected winner does not cross the finish line first, and the biggest upsets in Kentucky Derby history have paid out bettors very generously.
In 1913, Donerail astonishingly won the Kentucky Derby with odds set at 91-1 giving bettors a hefty return, but the odds were a result of a fairly new parimutuel betting system. In 1908, Kentucky outlawed bookmaking and Churchill Downs had to return to the system that was experimented with decades before. Heavy wagering on the two favorites, Ten Point and Foundation, produced the longshot odds, and Donerail still holds the Kentucky Derby record for the longest odds to win.
In 2009 on a sloppy track, Mine That Bird had one of the most notable upsets in Kentucky Derby history. After starting off slowly out of the gates, he came out of nowhere and blew out the field in the final stretch winning by 6 3/4 lengths. Mine That Bird had the third-lowest odds in the field at 50-1 despite 2007 Kentucky Derby winning jockey Calvin Borel being on board. The thoroughbred never won another race after that in nine more starts, finishing second in the Preakness Stakes and third in the Belmont.
One of the most controversial Kentucky Derby finishes led to another huge upset in 2019. Maximum Security crossed the finish line first but was disqualified after the race for using an illegal move. The second-place horse, Country House, was named the winner and had 65-1 odds. It was the first time in Kentucky Derby history that a winning horse was disqualified for an illegal move on the track. The disqualification was appealed, but ultimately the ruling was upheld. It was costly for many bettors as Maximum Security was a 9-2 favorite, but Country House etched his name in the history books with the second-biggest upset in history.
While those horses were obvious underdogs to win with their longshot odds, there were also notable heavy favorites who choked in the first leg of the triple crown.
Before the 1953 Kentucky Derby, Native Dancer was undefeated in his first 11 starts. He was the subject of a lot of media attention and came into the Derby with 3-5 odds as the heavy favorite. However, Native Dancer ended up losing to Dark Star, who was mainly disregarded with 25-1 odds to win. In Native Dancer’s career, the 1953 Kentucky Derby was his only loss in 22 starts. He is considered a legend in horse racing and was eventually inducted into the National Museum of Racing and Hall of Fame in 1963. Dark Star ended up suffering a career-ending injury two races later in the Preakness Stakes.
The 118th running of the Kentucky Derby in 1992 featured Arazi, a French horse who also gained extensive press coverage and was declared by some to be the second coming of Secretariat. He was the clear-cut favorite to win with 4-5 odds. He drew the infamous 17th gate that has not seen a Kentucky Derby winner yet to this day. Not only did he lose, but ended up finishing in eighth place, which was the worst finish for a Kentucky Derby favorite in history, as Lil. E Tee won the Derby at 17-1 odds with the slowest time in 18 years finishing in 2:04.